4.8 on September 28, 2016
Our wedding in September 2016 was absolutely incredible and Great Oak Manor was the star of the show (besides us of course). Spending the weekend and having a place where our family and closest friends could stay with us was invaluable. The house is spectacular and fits perfectly with the beautiful grounds. It was fun deciding which of our relatives and friends would stay in each of Great Oak's large and welcoming rooms. Our ceremony was by the water, complete with bay views and a nice sunset. The back yard was a great setting for our cocktail hour and the side yard was prefect for our seated dinner and dancing. The staff couldn't have been more helpful all throughout the process, and especially during the weekend. A huge thanks to Great Oak and the team for a truly unforgettable wedding for us and all our guests!!
5 on June 18, 2016
Outstanding in all categories. The breakfasts are a delight, and full of surprises. It is remote enough to be out of the beaten path, but close enough to Chestertown and Rock Hall to enjoy equally outstanding dinners. There is a friendly and helpful staff if you should need anything. The rooms are of equally high standards. It would be difficult to find a better setting, with grounds on the Chesapeake Bay for relaxing and watching the sunsets over the bay. Highly recommended. Gene Larson
5 on November 19, 2015
Beautiful property, great service, fantastic views of the Chesapeake Bay. We are already planning our next visit. H. Sheneman
3.8 on October 08, 2015
The staff and Innkeepers were lovely and very helpful. Everything was just as stated on the website.
5 on August 24, 2015
Been to the manor twice and was best ambiance and environment I have ever experienced! Recommend you stay there it will set the standard you should expect from any provider in the industry!
4.6 on August 12, 2015
Everything was great! The staff was very courteous and helpful. All food preparations were unique, well prepared and presented. Love the old charm and country feel. Wonderful weekend getaway, looking forward to our next stay during the week.
5 on August 05, 2015
What an incredibly restful place, and so close to Washington, D.C. We stayed in the Roese Room, and the pet-friendly policy allowed us to bring Lucy. The staff were great. We are telling all our friends about The Great Oak !
5 on June 16, 2015
My favorite place in the world to paint and watch birds. Amazing staff, best breakfast I've ever had at a B&B worldwide. Best view. Can't say enough nice things about the character of the building, furniture, library and did I mention VIEW! Eagles, kingfishers, herons, warblers, turkeys, etc. Binoculars provided! Can't say enough nice things about the Inn, Innkeeper, staff, rooms. Favorite place on earth to paint.
4.6 on May 30, 2015
A wonderful stay at Great Oak Manor! Beautiful guest rooms, with new comfortable bedding. Lovely new wallpapers and paints. Helpful staff. Tasty breakfasts. Gorgeous sunsets. Great water views. Spacious grounds, terrific for strolling along the shore. Close to historically, architecturally interesting Chestertown. Charming!! Barbara Thompson
5 on April 08, 2015
I just returned from a wonderful two stay at the Great Oak Manor Bed and Breakfast. It was so relaxing! The view and sunset was spectacular! The new owners have up dated in and around the Manor. The one improvement was new bedding and linens.The Innkeeper was very friendly and happy to satisfy your every request. She served a fabulous breakfast and dinner. You feel like a special guest. Eileen Kuhn
4.8 on December 26, 2014
We had a great 2 night stay prior to Christmas. The house was decorated very well and property is just breathtaking being located on a former large estate. The host was outstanding and was extremely attentive and informative. She made sure all amenities were at our disposal and helped set the mood for a very relaxed experience. Being fairly secluded outside of historic Chestertown , you really got the sense of stepping back in time to a simpler period . Would highly recommend the in-room couples massage experience.
5 on May 15, 2013
Incredible view - fantastic manor - wonderful innkeeper! Incredible breakfasts! MY FAVORITE INN IN THE WORLD!!!! Time stopped for us. Bring a great book or catch up on your magazines as there are many chairs and some hammocks that say "sit, stay & enjoy!!!"
3.8 on August 19, 2012
My husband and I have been visiting Great Oak Manor for over 20 years. During that time the property has changes owners three times. It is always a pleasure to find that the lovely B&B stays as gracious and beautiful throught out the transitions. With beautiful rooms and friendly staff, rolling back lawns that meet the Chesapeake bay, hammocks and lounge chairs to sit in while one reads or watches the eagles and osprey fish, or puttering round Chestertown and near by Rock Haall, Great Oak Manor is a perfect get away, oh and yes, breakfast is yummy as well!
4.8 on June 24, 2012
We experienced a beautiful weekend stay at the Great Oak Manor! It was the perfect venue for a quiet yet fun celebration for our anniversary and my birthday! The rooms are gorgeous and the complimentary breakfast is delicious! A great place to just BE.
4.8 on June 03, 2012
Meticulously maintained, beautiful decor in a beautiful setting. Outstanding service as well. The property is off the beaten path but a short drive to historic towns and other attractions.
4.6 on May 27, 2012
My husband and I spent 3 nights at Great Oak Manor in May. We wanted a beautiful place on the water that was peaceful and quiet. And that is exactly what we had! The public spaces are elegant but comfortable. Breakfast was cooked to order every morning. We even saw a lovely sunset on the first evening. The staff was very friendly and extremely helpful. We will definitely go again!
4.8 on May 20, 2012
Stayed three nights with relaxation, friendly helpful staff and delicious breakfast. Definitely recommend.
5 on May 04, 2012
My wife and I stayed at the Manor in April 2012. Know what you are looking for: this is a somewhat remote, beautiful, serene gorgeous place. No miniature golf, no neon, no nonsense. But "Wow!" Just beautiful. On the Chesapeake Bay. With, incidently, beautiful Persian rugs.
5 on February 28, 2012
Although it was only for 1 night, it was the perfect stay. We were greeted when we drove up by Cassandra and Charlie (tail wagging) and I immediately felt at home. After a tour of their beautiful home, showing us where everything was. Our room was beautiful and after settling in were spoiled by a nice tray of cheeses and fruit before heading out to dinner. After a great meal in Chestertown, we came back to our room and enjoyed the fireplace in our room and quiet time. We awoke to a beautiful view outside our room of the river and enjoyed a wonderful breakfast with eggs and fresh blueberry muffins. Excellent service and hospitality. Thanks to all for making our short stay a memorable one!
4.0 on February 01, 2012
We love this place, in winter and summer both! It is so relaxing!
5 on November 13, 2011
Cassandra and John are terrific! We have stayed in their "home" many times and always look forward to our next visit. Their friendliness is genuine and Cassandra runs an awesome inn! Thanks! Beth W
3.4 on October 31, 2011
Great Oak Manor was delightful. It offered a very quiet getaway for a very busy couple.
4.4 on October 26, 2011
Short two night stay was terrific. The location is wonderful. Innkeepers and staff were very friendly and attentive..... The Inn was exceptionally quiet and restful. On our second night we were the only guests there so it was VERY quiet. We would recommend staying there to anyone.
4.4 on October 24, 2011
The big pull to this B&B was its location right on the Bay. The pictures on the web don't do the view justice. The back yard goes straight out to the water and provides a relaxing place to nap, read, or just take it all in. We really enjoyed the feel of the house and property. The hosts were very pleasant, and the breakfasts were delicious and more than sufficient.
4.8 on October 13, 2011
We had a lovely stay at the Great Oak Manor. The rooms were beautiful, the service and food were amazing. The grounds are expansive, but show some signs of needing attention, dying trees and outdoor chairs covered with moss and lichen. But the breakfasts were amazing, worth the entire trip!!
4.0 on September 18, 2011
Great Oak Manor is a 20-minute drive from Chestertown and about 30 minutes from Rock Hall. That makes it somewhat inconvenient for evening dining, but for a complete Eastern Shore getaway, it is superb. The house itself is beautiful, the rooms extremely comfortable, the views serenity-inducing, the welcome and service excellent. Breakfast is abundant and elegantly presented. Lawn chairs, loungers and a gazebo offer ample opportunity to gaze out on the Chesapeake Bay.
3.0 on August 29, 2011
We just returned from a relaxing getaway at Great Oak Manor. The owners, Cassandra and John, both welcomed us personally and greeted us every morning. The grounds are beautiful, with an expanse of lawn that instantly relaxes you, incredible bay views and a beach to stroll down as the evening winds down. Bird watchers have the added bonus of an eagle's nest nearby so you can watch their comings and goings. The bedroom was comfortable and clean, though you could hear people next door and on the floor above. And for Chestertown, the price was a bit steep compared to other very nice stays, like the Brampton Inn, which are closer to town. Still, we definitely enjoyed our stay and would recommend it as a getaway for anyone who can afford to stay there.
4.8 on August 25, 2011
Great Oak Manor is, by far and away, our favorite B&B. We've stayed there many times and, when we have a couple of days to relax, there's nowhere else we'd rather go. Thanks Cassandra, John and the rest of the staff. It doesn't get any better than this!
4.4 on August 17, 2011
I had a wonderful stay at Greak Oak! The staff was incredibly helpful and personable. The Manor was beautiful - with lots of different spaces to experience and enjoy. The back lawn and view of the Chesapeake is breathtaking. I will definitely recommend this place to family and friends and hope to return in the future!
5 on August 16, 2011
My husband and I stayed here for a romantic and relaxing weekend getaway. It was perfect! Apon arrival, we were told that the room we reserved had an odor. They let us see the room to determine if it was ok, but they quickly added that we could have an upgraded room an no extra cost due to the problem. The upgraded room was wonderful. Each morning, we had a great breakfast buffet of fresh fruit, yogurt, cereal, and baked goods. We would take our food out to the beautiful patio overlooking the bay and their resident bald eagle. At that point, a lovely woman would come out and take our order for the hot portion of our breakfast. The food was very good. It was hard to be hungry for lunch after that. The manor itself was so beautiful. It was very hard to leave. I would recommend this bed and breakfast to anyone looking for a relaxing stay.
4.2 on August 14, 2011
We had an amazing short weekend stay at the inn this summer. The attention to detail was what really made our stay memorable - snacks in the afternoon, great service at breakfast, amazing linens on the bed. The staff was friendly and helpful. They were easily reachable, but not intrusive. With best intentions, the staff's dinning recommendations were a little off. We got the sense that some of the places they had recommended were places they had never visited, yet dinned at. When we came in Friday and wanted an easy, "casual" place to eat at, we found ourselves, through a staff recommendation, at a place with "fine dinning" on the sign and prices ranging from $25-$30 an entree. Other than that, we had an amazing time and have already encouraged friends and family to book at the Great Oak the next time they are looking for a relaxing weekend away.
5 on August 12, 2011
This is our favorite B&B. The location is beautiful -with eagles flying around the grounds. The owners are so helpful, the breakfast plenty and delicious, and the rooms comfortable.
4.0 on August 10, 2011
The view was spectacular--the photos on the website didn't lie. We had a wonderful, relaxing stay at Great Oak. Everyone was pleasant and helpful and Cassandra's restaurant suggestions were excellent. Attention was paid to detail, which is why we love to stay in B & Bs. We highly recommend Great Oak and hope to return.
5 on August 09, 2011
Literally you will find much peace and relaxation here. The Inn is so beautiful, with every amenity possible. The grounds are simply breathtaking with your own private beach, to enjoy. Cassandra, John and their staff go above and beyond to make their guest feel special. I think this Inn is the best kept secret on the Eastern shore, we will be back for sure.
5 on August 09, 2011
This is a simply exquisite manor home. They was nothing that could have been done better, from the grounds, the common rooms, our beautiful suite, and outstanding food! Just 90 miles from Washington DC. I am already looking forward to our next visit. Catherine C. Chevy Chase, MD
5 on August 09, 2011
Beautiful. Peaceful. Cared for without any nagging. Feeling like you've touched a part of history. All for a very reasonable price. If you have the opportunity, do not miss it.
4.0 on July 29, 2011
We live outside of Philly and had to drop my 13-yr-old daughter off for a week of summer camp in Chesterbrook. Rather than just dropping her off and driving straight home again, my fiance and I decided to treat ourselves to a night's stay in town. When we travel, we ordinarily don't choose accommodations quite so luxurious as Great Oak Manor. But it also happened to be my fiance's birthday ... so we decided to splurge. We really enjoyed our stay. The young staff member who greeted us and got us situated was really friendly and made us feel very welcome. The room and the entire estate and grounds were beautiful and exceedingly comfortable. We loved the robes! And the private beach ... which we were spoiled to have entirely to ourselves. And Charlie, the sweet, quiet, golden lab who made us laugh by eating a cucumber from the garden while we were there. We're hoping that my daughter decides to go to the same camp in summers to come so that we'll have an excuse to make a tradition of a summer stay at Great Oak Manor.
4.0 on July 28, 2011
Loved being on the Chesapeak Bay. Rocking chairs by the gazebo were a great way to view the boats going down the bay. Enjoyed early in the morning (Monday) watching the crap traps being put in the water. The breakfast was a real treat. Cassandra was a great host, very helpful in recommending places to dine.
4.0 on July 26, 2011
We thoroughly enjoy our stay at Great Oak Manor Inn.....It definitely did exceed our expectations! The room was delightful and the view was beautiful! Breakfast was wonderful and the Innkeepers and staff were friendly and helpful. We would definitely return to this B&B!
4.4 on July 25, 2011
If you are looking for a place to get away and relax this is for you. Feel pampered, experience quiet and de-stress. We truly enjoyed ourselves. A good book and a few days is all you will need the peacefulness will do the rest.
4.6 on July 13, 2011
Wonderful grounds, very friendly staff, very relaxing environment. Highly recommend!
4.0 on June 19, 2011
Everything was exceptional. The innkeepers went out of their way to ensure our entire vist was perfect. Beautiful grounds and rooms. Breakfast was acceptable but not as outstanding as the rest.
5 on June 18, 2011
As you drive the country road leading to Great Oak Manor, you can imagine what the once-massive estate encompassed when it drew luminaries such as Guy Lombardo, Robert Mitchum and Jack Kennedy. The road segues from sunny to serenely tree-lined and shaded as you approach, and then it suddenly comes into view. Reminiscent of European manor homes, the inn stands majestic at the top of a circular drive. We had visited the previous month and couldn't wait to return, lured by the house and it's lovely views of the Chesapeake from the back yard. It's the ultimate place to sit under huge shade trees and watch boats pass by. Charly, the golden retriever and co-host of Cassandra Fedas, will welcome you with a friendly wag. The entertainment isn't confined to the water - birds of many varieties sing and soar overhead. If you are looking for stainless steel and modern decor, this will not be your cup of tea, but if you love the elegance of days gone by, you will find that and more. In a nod to modernity, the conservatory offers a bright open room to enjoy day or evening, and a good place to observe the water on days that are less than optimal, weatherwise. The endless lap pool is also here; look at the glass windows that surround it, particularly toward evening, and you will note renderings of birds in flight etched in the glass. It's always the weekend at Great Oak Manor where there are no traffic sounds and the service is always exemplary....even on Wednesday! Find your own little slice of heaven here on the Eastern Shore of Maryland.
5 on June 11, 2011
The house is authentic, stately, and very well appointed. Cassandra is gracious, friendly, knowledgeable, and very helpful.
4.0 on June 05, 2011
We had a 2nd floor room, which was very nice (except for the occasional stink bug). We had a room A/C unit which we used. Very nice deep tub in the bathroom. The property itself is gorgeous....right on the water with a huge "back yard". We enjoyed sitting watching the water (bring bug spray though). We only ate one breakfast there, but it was a good multi-course affair with a blueberry crumb cake, French toast and sausage. They have fruit and other snacks out during other parts of the day, and drinks were available as well. It was more expensive than other B&Bs in the area, but it is after all right on the water.
4.6 on May 31, 2011
We were there for our honeymoon and also to attend the Chestertown Tea Party
4.6 on May 26, 2011
We had a lovely stay during our son's graduation from Washington College last week. The Great Oak Manor is a wonderful retreat from the rest of the world. It exceeded our expectations in regards to the well appointed rooms, the cleanliness, the food and the friendliness of the Innkeepers. I'm looking forward to visiting again sometime in the future. We had a wonderful stay!!!!
3.8 on April 20, 2011
We had a terrific time - it's a beautiful property, and John and Cassandra are great hosts.
5 on April 16, 2011
Our stay at Great Oak Manor was rejuvenating. If you love a spectacular sunset over the water, this is the place. The house is magnificently appointed and the grounds are gorgeous and peaceful. Innkeepers and all staff are friendly and welcoming and respectful of your space. Cassandra is extremely knowledgeable and helpful in answering any questions you might have about dining and activities in town, and the whole Eastern Shore environs in general. Also, her crab quiche which we had for breakfast, is scrumptious. What a wonderful find! The Greens
3.0 on March 20, 2011
Great Oak Manor is a lovely spot. We had a pleasant stay but overall I was disappointed, given how much money we spent. The manor is an amazing building, and we received a tour of the property as soon as we arrived, which was great. The decor is all rather formal, the kind of furnishings that make me feel a little stiff and uncomfortable, rather than relaxed and comfortable. The room (one of the most expensive) was very clean, but the windows that look out onto the bay were very small. The small private deck that was advertised was very small, and with such a high railing on all sides that one felt rather pinned in. Breakfast was very nice, but nothing special or gourmet: fresh fruit, muffin, French toast, coffee, juice. Overall it was a pleasant stay, but for the price I paid, I expected much more.
4.8 on February 03, 2011
We had 24 hours for a relaxing escape from life in the city, and Great Oak Manor was perfect. The hosts were lovely, the room was comfortable, and we enjoyed the special evening of piano music, wine & hors d'oeuvres followed by a 5-course meal. We look forward to returning at different seasons to compare the scenery with and without snow.
4.0 on February 02, 2011
Enjoyable getaway and Saturday night dinner service. Owners and staff went out of their way to make our stay enjoyable.
5 on January 03, 2011
beautiful setting, fabulous house, wonderful hosts -- prettier than the pictures
3.6 on January 02, 2011
We always make it a point to come and stay at Great Oak Manor right after Christmas. This year, it was better because Great Oak is now "dog-friendly". The "dog-friendly" room was the Sterling Suite. While the room was not facing the water, it was convenient being on the first floor and had easy access to the expansive yard for our dog to play. Charlie (John and Cassandra's golden retriever) and our black Irish Wolfhound got along real well and all in all, we had a great time. Breakfast was also very nice, made-to-order eggs and a variety of fruit, cereal and pastrys. We'll definitely be back again soon.
4.6 on November 19, 2010
Approached by car on a sweeping pebbled road, The Great Oak Manor is majestic already. We were greeted by Cassandra, the Innkeeper, who was warm, sincere and attentive. The tour itself suggests she should be adding $100s more for the per night rate (ours was $179). Weather is no matter, for if it's rainy, there is an entire first floor of rooms open to the public, such as the library, the music room, and the open ballroom (?) complete with wading pool. And the rooms we peeked in and stayed in were beyond tasteful - they were a visceral calming place. The lawn is sizable and inviting. We passed the Adirondack chairs, the hammocks and the gazebo, taking the shell crushed steps to the river, and sat in the cozy bench, drinking champagne, and watching the sunset. BTW, the sunset can last an hour, with a vivid display. Sherry and port were served after dinner, where we met up with other guests. Breakfast was first class, beautifully presented and accommodating to guests who had egg allergies (Cassandra swiftly substituted with huge waffles). I purchased a massage, which occurred privately, yet on the premises, and concluded the best B&B experience I'e ever had -- in my fifty years!
3.8 on November 04, 2010
Our hosts were charming and friendly and extremely helpful. The house is gorgeous and the grounds are beautiful and the views of Chesapeake Bay are lovely. We had a very nice visit.
3.2 on November 04, 2010
The inn was very nice although in need of some minor repair for old leaks. Smelled a bit like mildew upon entry but otherwise was very nice. It's a lovely setting and the innkeepers do a good job of making you feel welcome. There is plenty of space to spread out and relax both inside and out. Our room was pleasant and had the amenities we expected. We would return if traveling in that area.
3.6 on October 20, 2010
My wife and I were down for our 1 yr anniversary. Room was very nice but not as romantic as we thought. We were expecting a little more for the money we paid. Hosts were very hospitable. Location is pretty amazing, right on the Bay. We were happy with our stay but we've had a better B&B stay elsewhere for less money.
3.8 on September 26, 2010
Our stay was perfect, but too brief. The setting is beautiful. The perfect place to unwind and get away from it all but close enough to get back to it all if you want to. The home is charming and the hospitality was great.
4.8 on September 22, 2010
Great Oak Manor is a little difficult to locate. I had to stop at a local store at which a helpful clerk provided the "back way" to the Manor,but once there, I was very impressed by the facilities, the amenities and especially the location. The manor house sits on 12 acres of Chesapeake bayfront with a gazebo and a small beach.Since the house faces west, the sunsets are spectacular. The view itself makes the stay worthwhile. The food was both excellent and plentiful.On the evening of our arrival , the bar was fully stocked, and a superior chocolate raspberry cake was the evening snack. There was absolutely no outside noise at night , but the adjoining county club did provide some background hum during the day. The inn even includes a recently added solarium with an indoor lap pool. Overall, 4 thumbs up!
4.8 on September 22, 2010
We spent an overnight weekend at Great Oak Manor. The views from the grounds and of the grounds were gorgeous. The owners/innkeepers were accomodating and helpful in many ways. The room was very clean and super comfortable. This was the first get away for my girlfriend and me, it was a memory we'll not forget for the rest of our lives. Since Great Oak is so close to where we live, we look forward to going there again and again.
4.4 on September 13, 2010
We spent a delightful fall weekend overlooking the upper Chesapeake Bay. The grounds are perfect, and the manor a gem. The nearby towns are clean and historic, with first class dining. The innkeeper, Cassandra, was extremely helpful, both before we arrived and while we were at Great Oak. We would go again.
4.6 on September 08, 2010
Great place to take your loved ones... The weather was beautiful and we didn't even spend much time exploring Chestertown because the B&B was so nice and secluded.
3.8 on August 24, 2010
A beautiful property and friendly innkeepers. My husband and I went for a getaway weekend and really enjoyed this property. We stayed at a few different B&Bs and this was our favorite. Although it's a large estate, you feel at home with the friendly service. There's tons of common areas inside as well as land outside to explore. It's the place to go if you really want to get away from it all (cell service is spotty) and relax which is exactly what we wanted to do. We definitely plan to return.
4.6 on August 24, 2010
The rooms are the largest I have seen in a B&B. The setting is magnificent, especially the eagles in the morning and sunsets in the evening. Best place to go to relax, unwind and rejuvenate. Great food and service. 5 star.
5 on August 22, 2010
The Innkeeper, Cassendra is a wonterful hostess! She is eager to accomodate your needs, make recommendations on restaurants and local activities, and welcomes you with a delightful snack in the guest kitchen to include cookies, fresh watermelon, ice tea, and ice water. There is ice and ice buckets available to take to your room as well as a full refrigerator for guest use--a great place to store your favorite wine or beer! The rooms are just lovely and the beds very comfortable. The views of the bay are not to be missed! Chestertown is a fun little town with lots of great restaurants and activities. We are planning our next trip!
4.4 on August 21, 2010
We were only able to stay one night because of work obligations, but it was such a memorable stay. The grounds are so lovely and relaxing, the staff amazingly friendly, and the rooms, gorgeous. I would recommend Great Oak Manor to everyone.
5 on July 23, 2010
Beautiful setting on the Bay, wonderful historic Mansion and teh most gracious innkeepers ever! My favorite - have stayed there EIGHT times!
5 on May 05, 2010
I've stayed at Great Oak Manor 3 times and each visit is one of the most pleasant weeks of my life. Everything about the Inn is perfect in my opinion. The wonderful hosts, John & Cass, make you feel like it is your home. If only it were, I'd never leave. The breakfasts are incredible -- home-baked muffins, coffee cake, quiche or other tempting treat every day. The rooms are decorated elegantly but are completely comfortable. The grounds and views are among the best on the Bay, which is saying a lot. I look forward to going back every year.
4.8 on April 28, 2010
Having just returned from Great Oaks Manor we have nothing less than glowing comments. The innkeepers made us feel totally at home and ensured we were both settled in and fully informed on activities at the inn and in the surrounding area that would be taking place during our visit. The grounds and buildings are immaculately maintained. Especially pleasing was the abundance of soft towels in the bath along with a full range of toiletries. We were able to participate in the last of the Spring 2010 series of catered, gourmet dinners. The dinner was preceeded by a musical presentation by an exceptional pianist who entertained the guests while we enjoyed hors d'oeuvres and wine. The dinner consisted of a five course meal with wines specifically paired with each course by the innkeepers. Following dinner we adjourned to the library for coffee or tea and lively conversation with our hosts and fellow guests. The experience was reminiscent of a more leisurely era where an evening consisted of the same elements: superb food, excellent live music, and great conversation. We would recommend Great Oak Manor for all but families with young children since the inn is decorated and the activities are geared to adults. It is especially suited for a romantic getaway for two or for special family events such as a reunion or wedding anniversary celebration. A stay of several days would enable visitors to fully appreciate and explore the Eastern Shore of Maryland and its myriad of small towns, great restaurants, and friendly residents. Great Oak Manor is well worth a visit.
5 on March 22, 2010
My friends and I have been going to Great Oak every year for over 14 years. When John and Cassandra took over 7 years ago, we were afraid our experience would change. Well, it has...and it only gets better! Friendly, accomodating and helpful. Won't get better views or a more charming location. Wonderful breakfasts...and the Gun Room is always serving coffee and other refreshments. We never tire of going there!
4.4 on January 01, 2010
This was our second visit to Great Oak in three years and we were so enthused about it that we took another couple with us this time to share the experience. Cassandra and John treat you like family. They are genuinely interested in making your stay at the inn and your visit to Chestertown both memorable experiences. Breakfast was plentiful and delicious; and the afternoon snacks were yummy. We will definitely return as soon as we can.
4.0 on November 09, 2009
Have just spent a wonderful week-end with friends and family at Great Oak. John and Cassandra were the perfect hosts. Staying in their beautiful home was a joy, the house was magnificent, and the views of the bay perfect. We recieved such wonderful attention from our hosts, from the moment we stepped into the front door. From food and drinks, and all the other extra details, would highly reccomend Great Oak for anyone looking for a quiet retreat.
5 on October 16, 2009
We chose to have our wedding and reception at Great Oak Manor. It was the perfect setting. Our family and bridal party stayed with us at the inn which made it very intimate. John and Cassandra were the perfect hosts. Infact, they were more like family. We hope to return every year for our anniversary!
5 on September 17, 2009
We just married off our only daughter and needed a retreat! Steve and I experienced the Great Oak Manor last year...so my search for the perfect B&B was over!!! Naturally, we headed to GOM for our get-a-way. We also celebrated our 38th Wedding Anniversary there! God willing, we will continue this trend for our Anniversary celebrations!!! Rita L.
5 on March 25, 2009
We arrived in a caravan of cars and vans for our 12th consecutive annual weekend of pampering at the Great Oak Manor; we are welcomed like family coming home for a visit by John and Cassandra. We are a group of 15+/- ladies calling ourselves "C.H.A.O.S." (Crop Happy Addicts Of Scrapbooking) who gather yealy to relax and indulge ourselves the beautiful manor and surrounding grounds. We work on our scrapbooks, read, crochet, quilt, and just relax. This is the one weekend a year that is "ours" and we are spoiled and catered to all weekend long. We have come to look upon Great Oak Manor as our home away from home and when the weekend ends we are already looking forward to the following year.
4.0 on March 06, 2009
We recommend this Inn to anyone that loves great food, fine wine, terrific music, beautiful scenery, friendly innkeepers and luxurious spaces. We loved every minute!!!
5 on February 08, 2009
We wanted a quiet, relaxing environment to escape and recharge our batteries. Great Oak Manor was all that an more. The innkeepers were unobtrusive but attentive to any way to make our stay more enjoyable. The accomodations are spacious and very well maintained. We regretfully left, refreshed.
5 on November 17, 2008
Such a beautiful place. All care is taken to make each guest feel spoiled. It's my new favorite B&B!
4.6 on October 02, 2008
Innkeepers John and Cassandra Fedas were so friendly and accommodations and made my visit so relaxing and comfortable. I didn't want for anything. I was able to relax and anjoy some quiet time as well as see the area! My visit was too short!
4.2 on July 23, 2008
Great Oak Manor is intimate, personal, and high end. If I told Cassandra that I wanted to have dinner at a particular place, she would dissapear and return with dinner reservations. Chestertown itself is a cool little college like town with a lot to offer, but I really wish I had a few extra days to stay in the gigantic mansion itself. You decompress at the Great Oak Manor, sitting bay side in a hammock with a glass of wine. The lap pool is fantastic, great way to start a morning before breakfast which you could eat in the dining room or out on the patio (which is where Cassandra would help you set up your day there) They delivered champagne to my room nightly with no issues and I was able to roam about freely in the massive site. Everyone met up around 7:00 each evening for port and sherry in the study which was such a pleasant plus to the experience. It's beautiful and it's relaxing and we are thankful we visited, as we will without question return to this site again and hopefully more sooner than later!
4.6 on May 29, 2008
The Great Oak Manor is a great place to stay. The manor house is wonderful, with beautiful views and places to relax. The grounds are extensive with many places to take in the views of the Bay. The rooms are very comfortable and the hosts will pamper you. I can't wait to return.
4.8 on May 26, 2008
Cassandra and John, my friends and I had a wonderful time at Great Oak Manor. We did not what to leave, but in our leaving we are truly inspired to spread the word of how wonderful our experience was at Great Oak Manor! The rooms were spacious and clean the private baths were huge and the grounds were breathtaking! Tonya Richardson
5 on May 15, 2008
The Great Oak Manor provided a great getaway from a very busy life. The innkeepers were a delight. What an enchanting place. We would love to return.
4.2 on April 30, 2008
We've had a wonderful week-long stay at the manor this april 2008. The location is gorgeous and the rooms absolutely lovely. Owners and staff went out of their way to make us feel at home. We highly recommend this B&B and would love to come back!
5 on April 30, 2008
The Great Oak Manor provided a great getaway from a very busy life. The innkeepers were a delight. What an enchanting place. We would love to return.
3.2 on April 28, 2008
My husband planned a surprise weekend getaway to celebrate my special "milestone" birthday. He selected the Great Oak because it looked to be a wonderful secluded place to relax and get away from the hustle and bustle of our busy lives. The grounds, the scenery and the home and its surroundings were beautiful, and very peaceful. However, we were not as impressed by the service. Our initial impression when we first arrived was not what we expected. After being on the road for over 4 hours with the first 2 in heavy traffic, we were looking forward to a relaxing weekend getaway. The innkeeper welcomed us by telling us she was just sitting down to dinner, then rushed us through a hurried "tour" of the home. This made us feel uncomfortable the moment we walked through the door, because we were imposing. Feeling rushed is exactly what we were hoping to leave behind. During our 2-night stay, the housekeeping staff removed from our room our fine crystal champagne glasses we brought with us. We brought them from England and they were a discontinued pattern. We did retrieve them, however, they were unfortunately run through the dishwasher. The staff also removed some water bottles we planned to keep (we purposely left them on the table and did not discard them in the trash can less than a foot away). I think the housekeeping staff should leave the guests' personal belongings as they are. All in all, the Great Oak Manor was a lovely place. Being awoken by a chorus of birds in the morning was one of the highlights of our stay.
4.6 on January 24, 2008
Restful, welcoming, friendly hosts. 5 star dinner. Elegant and tasteful.
5 on December 12, 2007
Beautiful ocean view b&b on the eastern shore. Great Oak Manor is a beautiful and peaceful b&b. The house is elegant and majestic, and the view is spectacular, over the Chesapeake Bay. The rooms are comfortable and elegant with nice modern ammenities. Breakfast is delicious, especially the manor muffins.
5 on October 14, 2007
My wife and I have stayed at B&B's around the world and Great Oak Manor is right there with the best of them. Ask Casandra to help arrange a crab dinner on the back patio. It was great and we will return.
4.4 on September 13, 2007
Our 4 day stay was absolutely relaxing. Beautiful surroundings, great host and hostess. Beat breakfasts, especially the crab quiche. We didn't want to leave! Helen & Joe
5 on September 02, 2007
This is the 4th time we stayed at Great Oak Manor and we will keep coming back. The house is gorgeous and every room has its own beauty and charm. The property itself couldn't be better as it faces the Chesapeake Bay as well as Fairlee Creek. What a wonderful place to come to relax and to revitalize yourself. The breakfasts are delicious and all the people are very friendly and helpful. What a total wonderful inn experience!
5 on May 16, 2007
I am part of a scrapbooking group consisting of 12 to 16 women who all share the passion of working on our family albums. This past March we celebrated our 10th annual weekend at Great Oak Manor. Each year we all look forward to our weekend away from all the streses in our lives. We are greated each year with big hugs from John and Cassandra as they welcome us to their home for a weekend of pampering and relaxation. This is the highlight of our year.
5 on May 10, 2007
Just like the Otis Redding song "Sitting by the Dock of the Bay, the Great Oak Manor has perfected the art of getting away by the bay. When asked by friends to find something wrong with our three-night stay all we could think of was that it was too short. The elegant accommodations, gracious hosts, friendly staff and delightful cats resulted in an enervating restful stay. The breakfast each morning was first class with warm muffins, fruit, yogurt, and a full hot meal that varied for each day. Having a parlor, library, solarium (with giant hot tub), sun room, and lounge as common areas all with very comfortable furniture provided a wonderful surprise. The many chairs, hammocks, and chaise lounges doting the manicured lawn overlooking the bay was indeed a vacationer’s delight. Having access to the executive length golf club next door was a real bonus. Being able to watch bald eagles, osprey, blue heron, and numerous other birds rounded out a complete relaxing occasion. The Great Oak Manor is not just for special occasions but is worth the visit anytime you want to get away and relax.
5 on February 04, 2007
My wife and I make it a point to go somewhere special on our anniversary every year. We had never been to a B&B before. Cassandra (the owner & innkeeper) was abolutely delightful, and made the weekend very special. We were very pleased with our room, and enjoyed the fireplace on our late nights talks. The food was absolutely fantastic. We had a 6 course meal that ranged from salad w/ goat cheese to crab imperial and duck. The service was top notch. I have since recommended this place to several of my friends. I guess the one word that would describe this place is WOW!